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Ibrutinib (Molecule of the Month for May 2017)

Imbruvica



Ibrutinib is used to treat cancers like mantle cell lymphoma, chronic lymphocytic leukemia, and Waldenström's macroglobulinemia, a form of non-Hodgkin's lymphoma. Ibrutinib is a drug that binds permanently to a protein, Bruton's tyrosine kinase (BTK), that is important in B cells.

Ibrutinib has been reported to reduce chronic lymphocytic leukemia cell chemotaxis towards the chemokines CXCL12 and CXCL13, and inhibit cellular adhesion following stimulation at the B cell receptor (BCR). Additionally, ibrutinib down-modulates the expression of CD20 (target of rituximab/ofatumumab) by targeting the CXCR4/SDF1 axis. Together, these data are consistent with a mechanistic model whereby ibrutinib blocks BCR signaling, which drives cells into apoptosis and/or disrupts cell migration and adherence to protective tumour microenvironments.

According to the Wall Street Journal in January 2016 ibrutinib, a specialty drug, cost US$116,600 to $155,400 a year wholesale in the United States. In spite of discounts and medical insurance, the prohibitive price causes some patients to not fill their prescriptions.

Formal Chemical Name (IUPAC)
(R)-1-(3-(4-amino-3-(4-phenoxyphenyl)-1H-pyrazolo[3,4-d]pyrimidin-1-yl)piperidin-1-yl)but-3-en-1-one

References

https://en.wikipedia.org/wiki/Ibrutinib

https://www.wsj.com/articles/patients-struggle-with-high-drug-prices-1451557981

Picture of Ibrutinib 3D model

click on the picture of  Ibrutinib above to interact
with the 3D model of the
Ibrutinib structure
(this will open a new browser window)

Picture of Ibrutinib

C26H26N6O2



Update by Karl Harrison
(Molecule of the Month for May 2017 )

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